Are you Sure You want This?

I first met Mike where we both worked as contractors for a Government agency. We shared a lot of things in common. We both hunted, fished, we both had a boat and we were both single.

A great friendship was born. We'd hit the bars after work many times closing them down. If one of us met a woman, well, it was every man for himself.

I'm John but my family and friends insist on calling me Johnny. I was 32 when Mike and I met. I played sports and actually started a agency softball team. I was in good shape. I was and still am 5' 10" tall and weigh 163 lbs. I keep my hair cut neat and just long enough to comb.

Like me Mike was also in good shape. He is 3" shorter than me and weighs 125 lbs. He was almost 40 pounds lighter than me.

Over the next few years I met and married what I thought was the perfect woman. Turned out she was a souless bitch who drained me of a lot my money, my energy, and my happiness. We divorced after 18 months of wedded hell and I swore to myself that I would be definitely more selective in the women I dated.

It was while I was married and near the end when Mike took an extended leave of absence from work. He'd never spoken to me about his plans and the first I heard about him taking off was in an email he sent throughout the agency. He didn't stop to say good bye or anything and I was left wondering what happened to my friend.

I called, emailed, and just stopped by his place unannounced. All of my efforts failed to reach him.

As the weeks turned into months and the months in a year I'd forgotten about Mike's sudden disappearance. My attention was on work and recent divorce.

After work one evening I was nursing a drink at the bar near the office. I wasn't interested in meeting any body even though I was newly single again.

I was stirred from my thoughts by a slim figure asking me if I minded if she sat next to me. I shrugged an uninterested, "do your thing," and tried to go back to my thoughts.

"Hi Johnny. I'm Annette."

Once again she had interrupted my thinking. "How do you know my name?"

She didn't answer right away and I turned to look at her. At first glance I thought she was kind of cute. Not beautiful but nice to look at. Her brown hair was shoulder length. Her brown eyes sparkled with a hint of mischievousness. She had nice full lips painted in a muted coral. Her breasts were small, waist narrow, and without making an ass out of myself I managed to notice she filled her bar stool seat very well.

But there was something familiar about her but I couldn't put my finger on it.

I pushed for an answer to the question I asked about how she knew me.

"I don't look familiar to you? she queried back.

I studied her closely and it suddenly dawned on me, "you're Mike's sister. Where is he? How is he?"

Annette gave me a coy smile, "Mike's gone Johnny."

"Gone? Where? How?" I thought my friend had died.

"Don't worry Johnny. Nothing bad happened to your friend."

"Please," I almost pleaded. "Tell me what's going on."

She placed her small soft hand over mine and smiled sadly. "Please don't hate me Johnny. Our beer drinking and girl chasing days are behind me now."

For a minute it didn't register on me what she was telling me. I stared at her for a minute before it dawned on me. "You're, uh, you're Mike?" It was more of a question than a statement.

"No Johnny. Mike's no longer exists. I'm Annette."

"But how, why."

"Lets move to a table Johnny, please."

"Let me buy you a drink first cuz I sure need one."

Annette wanted a vodka tonic and I ordered myself a double Jack Daniels.

We left the bar and moved to a small table in the corner. I sat first and noticed Annette was standing, waiting. "What's wrong?" I asked.

"You don't pull a chair out for a lady any more?"

"My friend wants me to treat him, or rather her like a lady," I thought.

I pulled her chair out and helped her slide close to the table.

"Thank you Johnny."

"No problem," I mumbled feeling strange. "So tell me every thing."

"It's a long story so please let me finish before you ask me anything. Okay?"

"Promise."

"Well long before we met I always felt something inside me was wrong. Johnny I know we hunted, fished and all that macho crap but my heart wasn't really into most of it. I was seeing a psychologist for years trying to find out what was wrong with me or what I was missing. During my last failed attempt at a relationship with Janice It dawned on me."

I took a long pull from my glass and singled the waitress. She came over and I ordered another double.

"One night after I failed to get and erection she fell asleep and I got up and wandered into my living room. I saw her clothes strewn about where we'd undressed. I was picking them up to fold them when it came to me. Instead of folding her clothes I put them on."

I guess my mouth was gaping open at that point.

"No Johnny I'm not a cross dresser as the look on your face suggests you're thinking. I'm in transition. For the past 15 months I've been under the care of a psychiatrist. I have been living as a woman and am taking hormones. I feel better about myself and am completely at ease at being Annette."

She drank her drink and I asked if she wanted another. "No. I'd better not. But please, you go ahead."

"Are you, I mean did you have um?"

"Are you asking if I still have a penis?"

I nodded.

"I do. That's the last step. I'm not sure I'm willing to go there Johnny. Yeah, I know. Even the head shrinker said I'm half stepping the process. But it is my body."

I finished my drink and told her I had to go home. "Sorry to run out but this is a lot to wrap my head around. You understand right?"

I pulled her chair out and let her walk in front as we departed the bar. I had to admit Annette had a nice ass. From the back she had the appearance of a woman.

Once outside she took my hand. I almost but stopped myself from pulling it away. My friend was looking to me for acceptance. I pulled her close and kissed her cheek. "It was nice to meet you Annette. Will I see you again?"

"I'm coming back to work next week Johnny. See you Monday?"

"Yes ma'am," I said as I bowed in jest.

I will admit I tossed and turned that night unable to sleep. I kept thinking about Annette and the changes I saw in my friend. I was ashamed that it bothered me that my friend had decided he preferred being a her.

The rest of the week past uneventful and since it was a rainy weekend I spent the two days cleaning my home and doing laundry.

I saw Annette Monday back at work. She had announced in an email to the entire agency that she was transitioning and for every one to call her by her new name. She caused a bit of a stir when she insisted on using the ladies room. She was forced to place an orange cone outside the door when she was using it and she was designated only one restroom in the whole building.

I caught hell from "the guys" for having lunch with her but fuck em. She was my friend.

We celebrated hump day with a happy hour. I began to feel different about her and the change from Mike to Annette. I grew comfortable with him becoming her and we settled into an easy conversation.

She asked about my marriage and I caught her up on the divorce and how much I loathed that cunt.

We talked about fishing and she said she would still love to go. We talked about hunting and she demurred. "I would love to go out on your boat and sun bathe though."

I asked how the hormones affected her and she explained that lowered testosterone caused her to lose much of her body hair and other changes she did not elaborate on. Other drugs were allowing her breasts to grow a little. I feel feminine Johnny. That may sound ridiculous to you but it's true."

"No," I interrupted. "I can see that. I can see that you're a woman. It shows in your walk, your face, the way you talk. I can see the changes Annette and I think you're very pretty."

We had another drink before agreeing to meet for dinner Friday night. "I'll stop by at 7," I promised.

Sure, we saw each other at the office several times and made small talk the next two days. I found myself looking forward to dinner with her on Friday. I was happy. I had my friend back. Even with the changes I accepted her for who she is. She knew me and I knew her... well almost but we were together again.

I was tempted to honk the horn outside Annette's place Friday at 7 but remembered the chair incident and went to her door and knocked like a gentleman.

I heard rustling and Annette call out, "just a second."

I waited patiently until she opened the door. What I saw surprised me.

Annette had applied her make-up almost professionally though I couldn't tell you what professionally applied make-up is. Her hair was done in an update version of a shag. Her out fit was tasteful and sexy at the same time. The little black skirt was not too short but a couple inches above the knee. Her blouse was white with just enough purple embroidery that it was pretty. She had chosen her colors well.

I noticed that Annette was looking down and her 2" heels and it dawned on me that she was waiting for me to say something. I gently put two fingers under her chin and raised her face so that she was looking at me. "Beautiful Annette. Very beautiful."

She pushed herself in my arms and started to cry. I held her close. I had no idea of what she was going through but I knew my friend was struggling. I kept my mouth shut and held her for the longest time.

Annette finally pulled back and sniffed. "Now I have to re-do my mascara," she said with a smile. "Thank you Johnny, I was afraid you would think I was some sort of idiot or clown."

"No baby girl," I said softly. "I meant what I said."

With a sigh of relief Annette said she'd be back in a few and left to touch up her face.

We ate and drank, talked and laughed and I confessed to her how lonely I'd been when she just up and disappeared a year and some ago.

"It was not my idea Johnny," she explained. "My doctor said it would be the best way. I missed you too but was so scared of what you would think."

I understood why that could be and let the matter drop.

We finished our meal and after our server returned with my credit card I assisted Annette out of her chair. It was a whim, only a whim that made me take her hand in mine. It surprised both of us but Annette and I walked out into the night shoulder rubbing shoulder.

When we got to my car I opened her door and as she slid in I noticed her legs. I'd been reluctant to pay much attention thus far thinking it would be gross. Her legs were nice. Shapely and long.

We got back to her place and she invited me for a drink. Now in the past I needed no such invitation. It was understood back in the day that we could make ourselves completely at home in her place or mine. No questions asked no permission needed.

I accepted her invite and once inside Annette poured her a glass of wine and me a double Jack on the rocks. I didn't know what to expect when she told me she was going to put on something more comfortable and waited anticipating God only knows what.

When Annette came back she had changed into a nice pajama set. It was very light pink as were her mule-type slippers. She settled in the chair across from me and tucked both her legs up under her. I could tell she was feeling one hell of a lot more comfortable being herself around me.

We drank well into the night and it felt like old times to us but different. In only a matter of an hour or so I knew I was sitting across from a real woman.

"What are you doing tomorrow?" Annette asked.

"I have no idea. Got any suggestions?"

"Your boat running?"

"Uh huh. Wanna go cruising tomorrow if the weather is good?"

"Sounds like a plan Johnny. Why don't you stay here tonight. You don't want to risk an accident or DWI."

She was right but I was unsure about the accommodations.

Annette saw through me in a flash. "You can sleep on the couch Johnny if that's alright."

In the morning she woke me with a cup of coffee. Annette had already dressed. She was wearing red shorts and a white spaghetti strapped top. I could see she was wearing a bra.

I did my morning ablutions as best I could and off we went.

Arriving at my place I brushed my teeth and changed into some shorts and a vented Colombia shirt.

With both of us in boat shoes we went to my pier and I started the boat. Annette had made sandwiches and grabbed a six pack from my fridge.

We cruised the creeks and river before heading out to the Chesapeake Bay. Annette stood near me most of the time and we talked about the times we had sea duck hunting and fishing for rock. We admired the large homes that were now the norm on Mill Creek and those that now lined the Patuxent River as we made our way down the swash.

I thought it would be a good idea to have lunch on Poplar Island and pulled up onto the shallow sand. We took off our shoes and hopped out.

I's put three CD's in the stereo on the boat and we listened to some soft rock while watching the boat traffic. I pointed over to Chesapeake Beach and reminded Annette how we once got so drunk in the Rod and Reel that the owner threatened to ban us.

"That was before old Gerald got gambling in there Johnny. We were lucky some of the watermen didn't want to kick our asses. We were pretty obnoxious that night."

"I remember it was fucking cold sleeping on the old boat too. I woke up shivering at first light wondering where the hell I was."

It was easy being together. I sat up on my knees and looked at her. Annette looked at me. We smiled and I slowly moved into her arms and we kissed. A short kiss on the lips and we both pulled back and looked at each others eyes. Then we kissed again more passionately. Her mouth opened to accept my tongue and hers explored my mouth as well.

Without thinking I pulled her top over her head. Her titties were little and cute behind her bra and I nibbled on them through the cotton.

"Oh God Johnny," she groaned. "Are you sure you want this?"

My answer was to kiss her again as I unhooked her bra.

Annette let me pull the straps down and off her arms watching for my reaction.

I went back to sucking her small budding breasts and took her by her ass and pulled her onto mine. We sat with our legs around each other kissing and me sucking her titties.

Annette unbuttoned my shirt and I felt her breasts against me for the first time. We held each other close and just talked and kissed. Most of what was said concerned what we were doing. I had to admit that if I thought about it I might have second thoughts. "Just lets go with the flow Annette," I whispered in her ear.

My cock was hard but I made no attempt to have her touch me. Nor did I touch her there. We just held each other happy in our companionship.

Finally the sun began to move into the summer time 6 PM position and I suggested we leave so as not to be cruising after it got dark. I know my way around the bay as did Annette but we also knew that weekends are for amateurs and nether of us desired to be put at risk motoring at night and getting hit by some drunk.

Back at my place Annette showered before I did. I pulled out a couple steaks and made a salad. When she was finished Annette had taken the liberty of borrowing a T-shirt and boxers of mine.

I showered, shaved, and put on boxers and a T-shirt too.

We drank wine, grilled steaks and ate. It was like old times but with a big difference. What had occurred that afternoon changed the dynamic between us. Annette felt more at ease being the woman she is with me and I felt more at ease being the guy trying to seduce her.

I saw her bend to load the dishwasher and admired her plump round bottom. From the back she looked sexy as any woman.

We went to the couch and Annette sat in one corner. I lay back face up in her lap. We didn't speak for the longest time. Annette then started running her hand under my shirt using her nails to tease me.

It worked. My cock sprang to life and poked it's angry self out of my boxers. I could feel Annette's little boner poking between my shoulder blades. I sat up and turned to kiss her. Once again she let me remover her top and she pushed me on my back and lay on top of me. "Is this what you really want Johnny?" she asked. "Are you sure?"

I answered with a kiss and our tongues danced a tarantella. Then Annette moved down my body and kissed her way to my naval. I felt her tongue on me and her hand on my cock.

I leaned up on my elbows. I always liked watching my dick get sucked. Tonight was no different.

Annette looked at me for permission. I took myself in one hand rubbed my cock on her face. She knew she had my okay.

She kissed the head of my cock tasting my leakage before helping me out of my boxer shorts. I pulled my own T-shirt off and eased back to enjoy my blow job.

I don't have any idea where Annette learned to art of cock sucking but she was an artist. She would bring me to the edge and back off. Again and again I humped and fucked trying to cum. Finally she let me.

Annette took my load, swallowing, savoring, and jacking my cock until it was spent.

I'd never had the urge or desire to suck dicks. I had been a puss hound all my adult life. But shit happens and things change. After my head cleared from the intense orgasm Annette had given me I took her in my arms and kissed her. Sure, I tasted my cum but was not repulsed.

I knew she would be hesitant so I very quickly knelt down and pulled her shorts off. Her hairless little dick was not much bigger than my thumb. "The hormones were doing their thing," I supposed.

Just before taking her dicklette in my mouth I looked at her and asked, "does this look like I'm sure?"

I sucked my first dick that night and I like to think I that everything my friend had worried about was drained from her tiny organ when she spurted her joy and relief into my sucking mouth.

We were inseparable after that weekend together. We pleasured each other orally until we were both worn out.

I was teased at work for the time I spent with Annette but like I said before, "fuck em."

I knew there would come a day... or night for that matter when I would fuck her sexy ass. Maybe I'd let her fuck mine though I doubt she could get her little self past my buttocks.

A year later it was decided that we were a couple. Annette moved in with me and no one in my circle of local Lusby friends knew that she had ever been Mike. We threw dinner parties, attended those hosted by others, and she became quite popular. We were a couple and when we got married no one was invited but they knew. Some how they knew. I think our license application was gossiped because when we returned from our honeymoon on the OBX our friends surprised us with the reception we never had.